A conversation with a design leader


Name: Steve Caddy
Location: Melbourne
What do you do?  I’m responsible for making sure people looking for houses with realestate.com.au have the best experience possible.

Job Title: I’m the Senior Manager, Property Seeker Journey, at REA Group.
Kids: Two girls and a boy – 9, 5 and 2 years old.

OK — you're a dot com era Designer (like me) — tell me about your time working in dot com:

Wow. That’s a big question. Where to start? It was a crazy, crazy time. I winged my way into the job and was lucky enough to have some technical competence, a lot enthusiasm and some good mentors (hello Jim!).

It was a very exciting time because the whole field was still fluid. We were babies, learning by playing. We were seeing what we could do – visually, with interactivity, with content delivery and information. On reflection, we were very often winging it. That was a lot of fun.

But there was also very little structure or support. Managers would fly in and out, we were left to our own devices and there was some horrendous decision-making. The forces that drive and kill digital businesses weren’t yet understood. UX practice, LEAN, Agile practice, experimentation culture, understanding conversion and network effects and habit formation — all that stuff came much later on. A lot of business cases were based more or less on some variation of “because internet!”

Your initial career path wasn't in Design was it? Talk to me — good, bad ugly:

No… Well, sort of. I was always into drawing, design and typography, and “computers” as a kid, and I wanted to be a designer who worked with technology. I had a sense that the internet was going to be big and an exciting space to work in.

In my final year of high school, my school’s a career advisor told me that design and I.T. (as we called it then) didn’t really go together and that I should choose one or the other.

I wasn’t the greatest at maths and loved design so I intended to go down that path, but then I broke both my arms in a stupid teenage basketball accident and couldn’t draw or paint.

Without a portfolio, a design degree was pretty much off the cards so I wound up studying computer science. In my second year I got involved in a business incubator doing 3D animation, and got some half decent coaching on business fundamentals. By third year I was pretty sure I didn’t want to do serious back-end development or software engineering, but I had that foundation.

When I graduated, I spent a week building a mock portfolio and applied for design jobs, and was able to bluff my way into the industry as a web designer. I bought the O’Reilly book on HTML on my way home from the job interview! 

(Note from Jim: I did the same thing with books on Actionscripting, HTML and PageMaker ;-))

My work was horrible, but I loved the studio environment and was fortunate enough to have some good guidance and patient mentors.

You've moved house five million times since we first met 18 years ago — what the fuck Steve?

I know. It’s a disease. It’s a long story. I joke at work that I’m trying to personally experience each of our consumer journeys – buying, selling, renting, building … — which isn’t true, but it has proven to be very valuable experience.

What were the last three books you read?

Hold Still by Sally Mann
Generation A.K. by Stephen DuPont
Inspired by Marty Cagan

What were the last three websites you visited?


What do you listen to whilst you're working?

Nothing these days as most of my work is with words now and I’m rarely at my desk for more than an hour.

What is the last TV Show you binged?

I don’t watch TV!

I’m resisting the urge because there are so many really great shows and I really don’t have time to dedicate to a new addiction. But I think TV is where most of the great on-screen story telling is happening now by the sounds of it.

A few years ago, I briefed you to write an article on [The Chief Meaning Officer](http://wearetank.com.au/work/cmo/) — apart from showing us both that a good brief will always create good work (wink wink) tell me about "meaningful work", what does that mean to you?

Haha. Well, to me it’s a balance of knowing where your values are and finding them in the work you’re doing. No work is meaningful all the time. I want to do work that I feel is good in the long run. Day to day frustrations come and go, but does what I do contribute to making someone’s life a little easier? Does it help make a more durable company? Does it make it easier for the people who work for me or around me to express their talents? Is it honest? Does it help others make good work? Will it last, and if it not, is it’s temporality a useful anyway. Am I working with good people? Am I learning? Am I teaching – and is what I’m passing on useful and does it increase leverage? Do I have time for my family? Am I supporting them?

And is this true in a 2, 3, 5, 10 year window? I think it’s important to do work you can sit with and learn from over an extended period of time. My experience is that good work, work that actually moves the dial, takes at least two years and quite a lot of reflection. It’s not as easy as the Medium articles make it out to be.

Meaning in my view, is as much something that you bring to your work than what you get out of it. Maybe more so. Definitely more so in leadership, because there are so many unknowns. You don’t have to change the world to make a positive contribution. Being too eager to change the world can sometimes hold you back.

You've had a stint in digital agency land where we first met, then a huge stint at Lonely Planet and another one now at REA. You've traversed the divided between agency-side, inside and outside — I'm interested in your point-of-view of the changing landscape for the consultancy/agency. What are the opportunities? What are the challenges?

Agency land was a lot of fun for me but, ultimately, I’m skeptical of the opportunity to do good work from within the agency environment, at least as far as products are concerned.

Most of the root causes of poor product design are buried deep within the firm. Do you remember that interview with Dieter Rams, where he talked about the years at Braun as being quite unglamorous?

To do good design, he said, you needed to work with finance, with materials, with procurement, with production, with marketing. That was a total epiphany to me. Good design is an expression of a lot of things going right inside the business as a whole.

What I have always wanted to do was make really good things. To do that you need trust, you need the right team for the problem, you need the right org structure, the right leadership, the relationships and channels of communication, the time to build a story over time, alignment to strategy, good management, maybe changes in partner relationships or contracts, revenue or cost structure or business model, priority, the things that people recognise as valuable, ways of thinking and so on. You have to make mistakes on each of those fields and correct course.

And the result of the best work is new IP, specialist knowledge, that the company employs over a time-scale that is years long and, if things go well, become culture. I don’t think it’s possible to do that from outside and, by definition, no smart company out-sources their core. It’s the people inside the company who need to decide how to shape their work, how it gets out, to see how it’s received, what it’s like to operate, to make sense of that and to go again. That’s the cycle.

An agency can give good advice, but it’s like coming to a motor racing team and running a workshop for the drivers, advising the mechanics, and pointing out where you think the quick lines will be. You can produce the team livery but you’re not the ones in the race.

Agencies and consultancies can and do provide good advice, an outside view, a broader industry view, or they might provide muscle in a particular competency that’s weak or not able to be prioritised internally – we’ve worked with some great research agencies for example.

Branding also benefits from a little distance I think. I do see good brand work coming out of agencies, but it’s not the work that builds companies or products, not in the long run, and that’s the work I love to do.

REA have an amazing internal capability — how do you create a culture of innovation?

I don’t think there’s an easy answer to that. Innovation is such a loaded word these days. I often think that the popular definition of innovation is something like high speed novelty.

The real answer is in Deming’s writings I think. Build quality in, look for the root cause of problems, stay with the really hard problems (sometimes it takes months or years), try to really understand the problem and what will be useful and valuable.

You have to think not just about what your customer needs, but how your company can contribute, if it can contribute, how to apply the strengths you have and be alert to the timing. Being first isn’t always best.

You have to have an environment where it’s safe to play, because that’s how you learn, but you have to take it very seriously as well. Watch little kids do this! They take their imaginative games very seriously!

Curiosity is extremely important at all levels. Why do people do that? What are the economics? What are the UX possibilities? What’s important inside the company now? Where are our constraints? What’s going on here? And especially for managers and leaders — what can I do better, how am I showing up for my team, how am I communicating. It all matters, even at a personal level: when you get feedback, it doesn’t matter if it’s true or not — isn’t it interesting that you’ve been perceived that way? What’s within your control to change that?

Agile methods, looking for value, the jobs to be done mentality, preferring conversation to documentation, cross functional teams, rituals like hack days and so on all help, but there’s definitely no magic bullet.

One thing that helps a lot is a having a culture where anyone can talk to anyone else about something that they’re interested in or have questions about, regardless of their level in the company or which team they’re a part of. That helps good ideas rub together and become pregnant with new, fatter, better ideas.

What does good creative leadership look like?

Spend lots of time understanding the context and locating the crux of the problem and make sure everyone understands those two things at every opportunity.

Give people room to go wide, but understand that you can’t ever know the answer before acting. You need to have a bias to action. Sometimes the team wants to go deep and explore, but you need a point solution this week. Sometimes the answer looks obvious but you’re drawing conclusions too early.

It’s important to have an opinion, but to be prepared to change. Use your believes to draw challenges out of others. Work with people one on one, then as a group and vice versa. Build a reputation as someone who can be trusted, and who cares, and use to buy your team room to move.

I believe that research is really valuable, but not more valuable than being able to work from first principles. Even if you’re in a complete vacuum of information, you should be able to come up with something based on some basic assumptions and build from there. How much information you get before pushing ahead with first-principles type thinking depends on how fast you need to go and the risk of screwing up. And this is the advantage of being client-side I think. Every experience you have builds context in your specific domain, so you do build up an intuition of what should work and what’s riskier.

Try to pass on what you’ve learned in your experiences. Make it safe for people to talk and express their concerns. Listen. Be available. Be human. Admit and accept imperfection, but keep working on getting better.

David Marquet had a great insight in recognising that giving people authority before they have the skill or the organisational context to use it effectively just sets them up to fail. In a complex business the right context can take years or months to build, and you need to focus constantly on trying to pre-digest that for new starters so that they can contribute more.

How important is being able to 'make stuff' for people in creative industries?

Hands on? I don’t think it’s vital — I know people who can’t write, draw or code worth much of a damn but they’re excellent conceptual thinkers and can get their ideas across. That’s the main thing.

It does help sometimes to be able to draw or code enough to demo an idea — prototypes are amazingly powerful for showing people what you mean and how it could be amazing.

That said, at some level the entire effort is about making stuff, or at least, about making the best stuff, the right stuff, or allowing it to be made and get to market at the right time.

What are you most proud of?

  • When my kids do the right thing when they have the option not to.
  • Learning to lead. My contributions to the teams I’ve been on and the teams I’ve been lucky enough to find myself a part of, I guess.
  • Working on something that millions of people use to do something pretty important in their lives, like find a home.

Tell me about one of your failures — how did you deal with it?
How did you overcome it?
What did you learn?

A couple of years into my product job here a PM and I discovered that the notes feature of realestate.com.au was barely used. We were trying to clean up the product suite at the time so we decided to remove it.

It turned out that although very few people used the feature, the ones who did really loved it. One guy was tracking a whole potential investment portfolio with it — including a log of interactions he’d had with agents and developers, calculations on expected rate of return, rental yields and depreciation schedules.

We found a way to do a database extract for everyone who sent us angry or upset emails. I wrote to each person explaining that I was the person who made the bad decision, explaining the rationale for the decision and apologising for how it impacted them — and here’s a copy of your recovered notes.

Most of them were actually very good about it and appreciated the effort. We reinstated the feature and made it easier to use in the end.

A longer failure was what happened at Lonely Planet. To be a great travel book publisher, it had become full of people who really loved to travel, really loved books and really appreciated authorship. The company had a deep love of book shops and backed them for too long. And we listened for too long to people who would tell us that they loved us and that we should keep doing what we were doing, even though they were no longer buying our product.

The bigger lesson there for me was the true nature of disruption. Slowly at first, and then all of a sudden, what seemed like tonnes (enough to fill a really thick book) of info seemed like not much at all (just a two-sentence description of a restaurant?!)

Having a huge physical distribution machine suddenly became a lot less valuable.

Learning to make money online was really hard. We didn’t know what model would work — advertising platforms and formats sucked even more than they do today and there was enough free writing in the blogosphere that early paywall experiments were failing like crazy. We were still in the era when there were big question-marks over user generated content — professional writers and editors couldn’t get their heads around what motivated people to write for free or why readers would trust strangers for recommendations. But they did.

In the end, the thing that dethroned Lonely Planet wasn’t some kind of new digital competitor, it was a network of information sharing and a missing business model that, like the Nothing in The Never-ending Story, destroyed businesses. The next wave of successful businesses came out of those ashes, but for a while there was not a competitor you could point to and say: “we have to beat them”.

There are other lessons too, but so many of the things I’ve taken away from that period are only apparent with the benefit of a few years’ distance. It’s only then that I think I’ve been able to kind of see what I think we missed and think about how that applies to the work we do and the landscape we operate in now.

One of the most critical skills in business today is to lean into all kinds of fear.

If you’re doing your job, you’re going to get an early hint of things that could ultimately put you out of business. When that happens, it’ll be a while before you know or when, or how or if you can do anything about it, so it’s a perfect fear-provoking storm. But you have to kind of get really curious about the threat, different ways to think about it, how it looks from different points of view and ways to tackle it based on where you stand today.

There’s a lot to be said for taking ownership and responsibility for bad calls. Doing that is the first step in correcting course and makes it ok for others to join you. If someone else is making bad calls it’s equally important to create an air of blamelessness so that you can get to a better, more creative space. It’s very rare that someone comes to work intending to make bad or stupid calls.

I’ve learned how important it is to be able to lead and manage your own perceptions, especially if you’re in a position where you need to lead or council others.

Who are you inspired by? Why?

The great people around me, because they’re smarter than me in ways that I’m not. There’s nothing cooler than working on something hard with someone who has a completely different set of skills to you and getting the best out of both of you.

I’m always impressed by people are grounded and happy and able to enjoy their circumstance.

Obviously people who are able to have outsized effects in their lifetimes (Musk, Jobs etc) are also very impressive — Musk especially because he’s so hell-bent on making big changes at scale, so determined not to be constrained and so good at applying leverage — but those efforts usually have another side to their coin. Elon’s ex-wife is on Quora, reminding people that massive successes can have massive costs in other parts of your life, and in the lives of those who live with you.

What are you inspired by? Why?

  • Compassion and play, because they makes such a difference.
  • How honest and curious kids are, and especially people who managed to carry that honesty, connection and sense of play into their adult lives.
  • Art, because it’s so pure and intuitive and the risks involved are so personal and necessary.

How do you keep your skills sharp?

It’s like anything else. Stretch. Practice. Get feedback. Reflect. Re-orient. Repeat.

I try to keep track of things I might need to know to be useful as the world changes, and make an effort to get curious about those things, even if they’re not immediately interesting to me at first look.

How do you ensure you keep learning?

I try to talk keep the company of at least a few people who think differently to me so that I’m challenged to do the same.

I don’t read a lot, but I try to make sure my reading (and listening) is really high quality and I try to make an effort to apply what I’ve learned so that it becomes practical knowledge. I want to read and listen to things that help me to think, not that just give me information. I love Ben Thompson’s Stratechery blog for that reason. The a16z podcast is also great because it offers an insight into the minds of people who have been through some really tough situations or who are leading in spaces that are evolving really quickly. I’m always interested to learn how they’re thinking and looking at things, and then trying to think about how that framing applies to our problems.

I find it’s very important to try to apply what you learn and reflect on it. I need to give myself some time for ideas to stew and bump into each other. That happens best with a clear head, so I try to keep from putting my mouth over the firehose of information that’s out there.

I try to limit my time on Facebook, Medium, and Twitter, and to avoid as many sources of things I supposedly can’t afford not to know because most of it’s just personal brand building or mind clutter. The reflection process is very important.

What are you doing to invest in your growth as a Designer?

Well, I don’t know that I’m growing as designer anymore in a professional sense. Even though I’m “out of the field” so to speak, I stay close to the designers in our teams who can talk to their work. It’s always interesting to hear about the way they’re thinking about their work, our problems, consumer problems, trends and interfaces.

My investments these days are in being a good design leader, because I have a small team of designers I’m responsible for and I them to feel like they’re growing and have my support to do their best work. I learn from them.

Tell me something about mentors and mentorship. Yes? No?

Absolutely yes, but not all the time.

Finding the right person for you at the right period in your career or life can make an enormous difference. I’ve had two or three managers who taught me so much just by the examples they set — just by watching how they conducted themselves, the way they managed the team and their own personal intensity, the relationships they worked to develop with the rest of the business.

Good mentorship is not unlike that teacher who brings a subject alive for you at school. You still have to do all the work, but they help you to open new doors in your mind and connect you to people and ideas that take you into new territory.

What are the key traits you look for when hiring new talent?

Self-management and self-leadership: Willingness to solve back to root cause instead of getting frustrated at complication — that includes seeking out new information and new constraints.

High confidence, low ego: A desire to really solve problems out in the marketplace and internally, which means staying in one place for a few years, building the product, getting the feedback, taking a misstep or two, connecting disparate ideas, pressing forward, owning and learning from failure and playing the long game.

A sense of urgency: Team fit — I think “10X performance” happens when you find yourself in an environment, with team mates and a problem that lets you work at your absolute best for a period in time. I want to build teams where everyone brings something important for that team at that time.

What's next?

  • Try to pass on the important things I’ve learned to my kids.
  • Be a good husband.
  • Keep doing the best work I can and enjoy the journey.
Jim Antonopoulos