Crafting a Creative Culture

We have arrived in an age of design. No longer relegated to a function of the marketing department or tacked on to an engineering process, designers are increasingly taking leadership positions in the top companies in tech.

But how do we manage creative teams to achieve their full potential? Jeff will share stories from my years of leading product development — both successful and not — to show that investing in culture might be the best competitive edge you can gain.

Jeff notes that we’ve been doing this a long time… Hotwired was 25 years ago!

Today Jeff’s talking about a key question, something that’s obvious a concern in his current role in a VC company:

Why do some products succeed when others fail?

Some people will say….

  • it’s just about distribution – if you get people to the product, you’ll be ok.
  • it’s innovation – tech people will tend to say this. Technology is what drives product success.
  • it’s about satisfying an umet need

In truth it is a combination of these things, there’s no single driver.

There is a truth that no product succeeds if it’s built by a single person – with some very very rare exceptions. Mostly the really big, successful products are built by teams. So ultimately it’s about the people.

What is it about successful teams? What can you do to minimise risks and maximise the chances of success?

You can try to gauge skills, team fit, experience… but the thing they’ve really been focusing on is emotional intelligence. EQ is “almost a silver bullet”.


Visualisation exercise: imagine you are enjoying a quiet paddle in canoe a peaceful lake, then suddenly you get flipped over into the water and you come up for air…

What emotions would you feel if you cam up and discovered some teenagers have snuck up and thrown you out, now they’re pointing and laughing. You’d probably be pissed off at them! But what if you come up and realise there was a piece of driftwood you didn’t see, that you hit and rolled the canoe?

You would have really different emotional responses to those two scenarios. You’ll have immediate reactions like gasping for air, but the emotional reaction is something you can control. It’s a skill called equanimity, or ‘grace under pressure’. A state of emotional stability, especially in a difficult situation.

Jeff talked through a morning where he found his kid ramming rolls of toilet paper down the toilet. As a parent you need to stay calm. And another scenario where TypeKit was having a major technical issue… publication to the CDN wasn’t working and things were backing up hugely. They discovered had launched and caused a sudden, huge spike in traffic. Then he found out there was more coming.

They had to work over the pre-Christmas weekend, which is part of the situation with a startup. It’s a risk. The team agreed this was one of those times they had to just get it done.

They had three days and decided to time box it:

  1. day one: identify the problem
  2. day two: build a solution
  3. day three: integrate and launch it

So they took a few steps:

  • sequester the team – literally something you can take from rocket science. They had one person on the dev team act as liason, and kept everyone else away.
  • remove business decisions from solving tech problems
  • provide moral support

They were trying to create a sense of equanimity, so people could perform their best in this moment.

They worked out in the end that there was a problem with their CDN origin server. They already had a plan to build their own origin server, to replace the stock one provided from their hosting partner. But the project plan for that was 19 weeks! But they did work out an MVP version they could ship in a day, that was just fast enough to bring the load back down and resolve the issue.

So what do we learn from all of this?

  • Everything we build on the web is connected, and everything breaks. We have to design for that – our teams, our infrastructure, everything.
  • Everything is user experience.
  • Teams thrive when they have a sense of equanimity.

Yesterday at Design Leaders, Project Aristotle came up a few times. It was an attempt to solve the question of why some projects succeed and others fail. They did it the Google way, by crunching a huge amount of data. What they eventually found: success came from teams who had a sense of psychological safety. That the team members had “a sense of confidence that the team will not embarrass, reject or punish someone for speaking up”.

It’s not just tech. Stephen Soderburgh says he likes to keep his set “relaxed but focused”. eg. with actors, he’s not trying to control them, he’s trying to amplify whatever it is about them that he finds compelling.

We are trying to create a culture of creativity. A creative environment where people feel safe, a sense of trust, a place they can succeed.

Comparing Adobe and TypeKit… Meetings! Adobe had so many meetings. TypeKit had some as well…

Meeting one: the standup – it was a way to start the day. Thinking back to Hill Street Blues – every episode started with the sergeant’s briefing, where everyone got into the room together before hitting the street. He’d always close with “be careful!”.

  • Start at 10:05 – don’t know why that worked, 10:00 nobody turned up on time; 10:05 they did
  • everyone attends
  • highly scripted event – many people wouldn’t speak
  • no phones/devices
  • no problem solving – take it offline

Meeting two: the product review

  • optional attendance, mandatory participation
  • not a forum for expressing opinions – this is crucial! Bad feedback: “I don’t like that blue”. Better feedback: “why is that blue?”. Great: “is colour important here?”
  • working session for group problem solving, that would be framed as either divergent or convergent. Is it a brainstorm trying to open up as many options as possible, or are you narrowing down to a solution?
    • divergent – brainstorming, limitless possibility, “yes, and…” (improv trick)
    • convergent – evaluate feasibility, acknowledge constraints, drive towards concensus
    • keep these two separate or they defeat each other

Things that work…

  • more exposure to users = better design instincts (designers, devs, sales people – everyone)
  • more exposure to great work = better design vocab
  • more diversity = broader product insights

You want a sense of candor – truth that is wrapped in compassion. You want to ultimately develop a team with good taste, a sense of pride in the work they’re doing, that they are making something good.

Meeting three: the postmortem

  • the meeting you wish you never had to have, where something has gone wrong and now you need to work out how to stop it happening again
  • a highly technical product has a lot of complexity, a lot of things that can go wrong. Nobody ever deploys code knowing it is going to break the system. They always thought it would work. But we have a human instinct to assign blame. It’s called fundamental attribution error – assigning mistakes to the character of the person and not the situation they were in.
  • Jeff got a lot of inspiration from Sakichi Toyoda, who came up with the “five why” technique for drilling down to the root problem. You are seeking the root cause.

Meeting four: the anti-meeting, group chat

  • acting like you’re distributed, even when you’re not
  • communication compression – chat can be shorter, more succinct than chat
  • ambient accountability – notifications of code deploys, PRs, support tickets, revenue events……animated gifs
  • gifs may feel frivolous, but it’s an emergent part of team EQ, teams that trust and care for each other. It’s less emotionally expensive to post Chuck Norris giving a thumbs up than it is to open say “you did great work, I’m really happy I work with you”


  • psychological safety
  • clear expectations for communication
  • empathy through exposure and diversity
  • circumstances > attributes (focus on root causes, not mistakes by people)
  • continuous accountability & appreciation
  • unified by a common purpose (why does the company even exist and what is it doing?)

There is a concept in Japanese culture ‘ikigai’, a reason for being (生き甲斐). There is a link between a person’s ability to express their purpose and their longevity. People with a clear sense of purpose, and the ability to express it, lived longer. In other cultures we have similar ideas like raison d’etre, devine will, nirvana.

Piglet: When you wake up in the morning, Pooh, what is the first thing you say to yourself?
Pooh: What’s for breakfast?
Piglet: I say… I wonder what’s going to happen that’s exciting today?
Pooh: They’re the same thing.

Our ability to write things down allowed us to have an experience and record it, so that knowledge could be transferred to others across space and time. We are developing new and faster ways to change data into information, into knowledge, hopefully into wisdom.

Now Jeff’s job involves trying to work out what’s going to be next. Designers craft experiences for the next generation. Can you find or create a team that makes you excited, where you can feel safe to create great things? Jeff thinks you can!