How We Boosted Creativity at OutSystems R&D

Tiago Simões
OutSystems Engineering
9 min readSep 26, 2019

Before anything else, take a minute to watch what’s considered to be the best commercial ever done by a tech company.

It’s from 1997, the year Apple was on the brink of bankruptcy and had to be saved by Microsoft.

Some theorize that the main target of the commercial was Apple’s own employees. Regardless of how true that may be, it surely had an impact on the company’s DNA and helped turn it into the mammoth it is today.

Do you know what I think?

I think it misses the point.

We’re all born creative, but only some of us continue practicing, and we can flex those muscles with deliberate practice. We’ll dig deeper into this further on.

Creativity Inside Organizations

How about organizations? Creativity seems to be such an individual pursuit…

Start by asking yourself: am I currently working in a creative company?

And then, follow up with another question that may answer the previous one: when was the last time someone asked me about what I’d like to work on?

We’re not talking about picking a task from the backlog or ordering it. A backlog is just a tool that helps us work together as a team. It gives us predictability, a guarantee of progress, and it assures that we don’t get blocked with questions like the ones above every single day. It’s one of the most important tools for mature organizations, especially in complicated projects with several dependencies. But it’s only a tool, only a box.

Do you know what’s the single most important thing you can do for your company when you arrive at work tomorrow morning? One thing I can guarantee — it’s not the next task you have on the backlog, and this may be a bit scary to realize.

You should ask yourself about what’s the best thing you could be doing for your company and your team. It may be a question that’s impossible to accurately answer, but it needs to be asked, and we should all try to answer it.

So, why hasn’t anyone asked you about what you’d like to work on (without a backlog in front or an agenda behind)? Don’t people trust each other? Don’t you trust yourself?

That’s the key to unlock creativity: a little more trust and a little more freedom.

Tips for Individual Creativity

To help you start moving in the right direction, I’ll share a few ways we’ve unlocked creativity here at OutSystems R&D. But first, some personal tips.

Guernica (Pablo Picasso, 1937, Oil on Canvas. Museo Nacional Centro de Arte Reina Sofia, Madrid)

1. It’s all about discovering problems, not solutions

We usually think about creativity as finding solutions to problems, but it’s the other way around. The best ideas come from people that fall in love with a problem no one else is worrying about. It suddenly starts being your problem, a problem for which you passionately care about.

2. Ask yourself: “What do I want to work on?”

First things first, you need to find the problems. One way to do it is by looking around. That’s why I love watching usability tests, why I love to listen to users, and why I love to follow what’s happening outside my company, discovering technical innovations that are solutions looking for a problem.

You can also take a step back and look at what you’re doing, to find repetitive tasks you can improve. I usually add these as bullet points in a personal document that I revisit once a month.

3. Protect your ideas

When you get ideas, you need to protect them. Don’t let yourself be brushed off by that person in meetings that has a strong opinion about almost everything. Don’t give up on a prototype just because someone was not as thrilled about it as you were expecting.

4. Don’t get too attached to ideas

You need to have confidence and pride in your work, but you also need to be humble, so you can actively listen to others. You can own the problem, but if you’re smart, you let others help with the solution. Feedback is always hard to listen to, as it usually involves more work for you, but if you listen to everything, it’ll help you create a stronger solution.

5. Embrace or challenge limitations

When solving a problem, you’re going to face several limitations. There are two ways to address them.

The first one is to embrace them. You have a single day to deal with a problem? See what’s the minimal solution you can provide to solve it. Limitations can boost creativity. For example, Guernica was painted in black and white, and maybe that’s why it’s such a colorful painting.

You can challenge those limitations and understand why they exist. For instance, does it make sense that you can’t change something because it belongs to another team? Can’t you just break the silos in your organization to solve a customer’s problem?

6. Don’t be afraid

Are you noticing a pattern? Look around and inside yourself. Protect your ideas, don’t get too attached to them. Embrace or challenge constraints. Those pieces of advice contradict themselves. Which brings us to the most important tip.

Don’t be afraid to contradict yourself. Innovation is always about contradicting existing concepts or beliefs. Being able to change your mind is the only proof you have one. Don’t be afraid of anything.

How Leaders Should Boost Collective Creativity

“Steve loved ideas and loved making stuff. He treated the process of creativity with a rare and wonderful reverence. I think he better than anyone understood that while ideas ultimately can be so powerful, they begin as fragile, barely formed thoughts, so easily missed, so easily compromised, so easily just squished.” — Jony Ive

So how can we protect ideas and make them grow?

Drawing Hands (M.C. Escher, 1948, Lithograph. M.C. Escher Foundation)

The people with the most responsibility are managers and leaders. The good ones have a hard time, as they are the ones on the front lines when something goes wrong, stressing out with project dates and with the need to deliver numbers. Having said that, here’s some advice for them:

1. Be positive

Congratulate people, thank them for their job. If at first, it feels fake, don’t worry, keep at it until it becomes second nature.

Once, there was a new product manager here at OutSystems R&D that looked at an early prototype and started by saying it was amazing. I could only think that it would compromise the product’s future and, even worse, that it had a tree. Our CEO hates trees.

What a wimp I was being. That lesson of positivity and celebration of proactivity was a breath of fresh air, and I knew that very well. That feature became the widget tree, one of the most used features in our product.

2. Embrace uncertainty

At OutSystems, our golden rule is “Ask why”. It’s the best rule ever. We’re responsible for understanding why we’re doing the things we do, always questioning their value. But when we’re in front of those emergent fragile ideas, what we should ask is “Why not?”.

It’s easy to get locked into plans and dates that we’ve already settled, overtaking the chance to do something different. What we know is safer than what we don’t, but it’s important not to be afraid of uncertainty.

3. Respect and leverage passion

Passion moves mountains. Even when that passion is of the shy kind, which is often the case with technical people. There’s always someone who’s seeing a problem that you aren’t, and there is always someone who’s working overtime because they’re worried about something.

Respect that.

Leverage it.

4. Ask: “What do you need to finish that?”

Pull prototypes and individual contributions to your team’s backlogs. People who work on individual initiatives usually don’t ask for time to complete those tasks. Often, they already feel guilty for working on unplanned projects. Take that step for them. If you sometimes have to surprise the team with new requirements, also let the team members propose tasks they feel are important when they start working on them on their own.

If you foster a culture where everyone listens to customers, you’ll start seeing virtuous cycles that create value without any additional effort from you.

5. Younger people and those with less context have bolder ideas

I see this happening on my team every day. Since I’ve been on this company for so long, I’m very cautious, and I find myself thinking: “We’ve tried that in the past and it didn’t work”, or “That is going to take a lot of effort”.

A good example of this is how much I worry about our existing users, even if I know we’re growing exponentially and the experience of new users can sometimes be more critical.

Younger people are less afraid of change.

Listen to them.

6. Set the example

Finally, as a manager and leader, it’s also your responsibility to set an example. Test odd theories, do stuff by yourself, set aside some time to work on crazy ideas, celebrate your failures. Just don’t try to push your ideas on others thinking that it’s the best approach. Creativity always comes from the bottom up. Give people the time and space for it.

Our Experience: MyFridays

Back in 2011, at OutSystems R&D, we started a program called MyFriday (loosely based on Google’s mythical 20% program) where you could take a Friday each month to work on whatever you wanted.

This was embraced enthusiastically by some, but soon that enthusiasm started to fade. Every once in a while a tighter deadline would loom over people’s heads, and we would compromise that creative time.

The last Friday of the month is ours.

MyFridays 2.0

In 2015, seeing this initiative slowly die, we switched it up with a very simple hack. We shared a talk about creativity (very similar to what you’re currently reading) and changed a very simple rule.

MyFriday would now be on a fixed date, the last Friday of the month. On those days, everyone would be working on MyFriday, turning peer pressure the other way around.

Here are the guidelines:

  1. It takes place every last Friday of each month.
  2. Find a problem you want to tackle, one that improves our product, our processes or our team.
  3. Do something — don’t just complain about it.
  4. Ask for help if you need it.
  5. Ask for feedback to iterate when you feel ready.
  6. Own the problem, not the solution.

If this seems more work, that’s because it is. Why would you do it? So you can feel and become more powerful; so you can improve your company and its impact on the world.

Wasn’t Creativity Supposed to be Fun?

When delivering this talk, I felt too prescriptive and negative. The slides were all in black and white. But then I realized why there was so much darkness.

We were growing at an incredible rate and we were at that turning point where companies lose their souls and start to slowly die. We’ve seen this happen all around us and didn’t want to follow their misfortune.

So, creativity is hard, but it was also the most important thing we had to do.

We could end up like those companies, or we could join the group of companies that continue to reinvent themselves and the world around them in which you can find the likes of Tesla, Netflix, Google, and Apple.

Have we managed to do it?

It depended on each one of us individually, but we did. From then on, every last Friday of the month, we each work on a completely different problem that no one else is working on. So far, it has been an incredible ride.

You can’t even imagine all the amazing small, medium and huge things that we are cooking up for the future!

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