How to Push Your Team to Take Risks and Experiment

13 March, 2017 / Articles

Most managers I know want their employees to be curious and experimental, to take the initiative and develop new products and solutions. But, as it turns out, managers also like to micromanage and control outcomes through safe, predictable processes. As a result, managers end up stifling the very experimentation they want to foster.

When Upworthy launched, we were berated for not using industry-standard practices. But two years and 50 million monthly readers later, Upworthy was barraged with requests for lectures and workshops on our “best practices” — and some of those requests came from past detractors. Ironically, we didn’t have a list of “best” practices; we simply had a practice of fostering experimentation by testing every piece of content. In fact, as our site grew I came to be suspicious of the very idea of best practices and got in the habit of saying: “Best practices are for amateurs.”

In my experience, the only way to encourage a team to be more innovative is to shift from a static, “best practices” mentality to a dynamic, “laboratory” mentality and to make each team member, not the manager, responsible for the results.

To accomplish this, managers can do four things:

Foster divergent thinking. Most people have an ingrained assumption that all problems have a single right answer, a mentality that most schools and workplaces reinforce. Don’t expect your staff to change that mental model overnight, or on their own. You’ve got to retrain them in how to think. I do this by employing a divergent thinking program.

Divergent thinking is different from creative thinking. It’s not the ability to come up with an original idea, but the ability to come up with lots of different answers to the same question. Divergent thinking looks more like insatiable curiosity than like original ideas. It is an essential skill for innovation because it provides team members with the foundation to create great tests. The goal is to gradually change a company’s culture from one of finding the right answer to one of exploring and testing many possible answers.

Every new writer on Upworthy’s staff went through a three-month boot camp, using a custom-designed curriculum that heavily reinforced skills in divergent thinking. The main component of the boot camp was drafting 25 headlines and generating eight to 15 images for every single story.

You can teach divergent thinking in a number of ways:

Ask your team members to come up with 15 solutions to a problem the company is currently facing.

Examine your company’s blueprints and ask your staff, from execs to interns, “How many ways could we rearrange our space to make our work more efficient?”

Make 20 mockups for every design change.

My personal favorite: If you are a manager, stop answering questions. Instead, respond with, “What do you think?” And then wait. After an answer is given ask, “What else?” And then wait. Repeat five to seven more times.

But the key to making divergence stick is to keep reintroducing it into the daily culture of your team. After completed the boot camp at Upworthy, our staff had free rein to publish on our site without approval. However, we encouraged them to continue drafting 25 headlines for each piece.

Make everyone responsible for their own tests. The most important lesson I’ve learned about implementing a testing culture in various corporate environments, media organizations, and startups is that the test results live inside the tester.

Segregating the person who generates ideas from the person who tests those ideas negates the ability of the ideator to learn how to craft solutions that resonate with the consumer. All team members must be able to test their own cockamamie ideas and see the results. This is experiential learning. And it’s how humans are hardwired to learn, iterate, and innovate.

Managers must set up a great testing culture and technical framework, but refrain from taking responsibility for their team’s outcomes, the good or the bad. Every single writer at Upworthy tested their own work. That meant they got to be the mad scientists in the lab, absorbing the lessons and accepting responsibility for the outcomes. If a writer had a big hit, that person got all the rewards and accolades. Not the team. Not the manager. The writer. If the writer bombed, it provided all the more motivation to try to “win” the next time.

Team members can’t take responsibility for what they can’t understand. Too many analytics dashboards are hard to navigate and display data in hard-to-use ways. At Upworthy, we made our dashboard more user-friendly by using visual cues like emojis, colors, and funny photos.

Team members can’t be responsible for what they don’t have time to do. Realistically, managers need to reduce their production expectations to free up the time needed to develop thoughtful tests. Depending on the complexity of your products, team members might be producing 25–75% less than others in the industry, but testing 100% of what they produce with the extra time. This is what I would expect to see in a company that is taking innovation seriously.

Empower your whole team with the support, structure, and time to do thoughtful, careful, creative testing, and you will see a culture of innovation flourish.

Normalize failure. No really, normalize it. How do you know whether your team is really embracing this new culture of testing? Set a baseline failure rate and success rate, and measure your team’s work by that baseline.

For example, at Upworthy, only about 1% of our content received massive engagement (relative to the level of engagement our content received on an average basis). The next 4% received very high engagement. The other 95% received average or low engagement.

However, the big, hairy, audacious goal at Upworthy was to make everything go viral. Many editorial staffers would mope in disappointment when 95% of their work fell below our aspirations. With that disappointment would come fear of failing. And fear inhibits creativity. The team started playing it safe. They relied on headline structures that performed well in the past and leaned into creating best practices to safeguard them from failure.

In order to break the “playing it safe” habit, the first thing the team needed to hear me say was, “A 95% fail rate means you are doing a great job! No, not just a great job — a fantastic job!”

For the whole company to succeed, smaller teams must have varying rates of success and failure. That’s how a company cycles through enough innovative ideas to arrive at a few successful ones. But often that looks like failure to insulated team members who may not be looking at the big picture every day. They become convinced they must be doing something wrong, which drives them to seek and implement best practices, as all the other “successful” companies must be doing.

The more that managers can normalize failure rates to align the team’s perspective with the reality of actual achievement and to eliminate fear, the easier it will be to innovate.

Testing and data should not be used to create best practices. The more tests your team runs, the more ideas they should get for new tests. Data should be generative, not conclusive.

At Upworthy, our goal with every piece of content was to discover the very best headline and image for that specific piece of content — not to discover rules to apply to all content. It is very hard to hold all this data lightly, to continually throw spaghetti at the wall, and to fight against the mind’s desire for simplicity and familiarity, especially when best practices may produce great results for a while. But if managers don’t establish a culture of continual optimization, the effectiveness of best practices will soon fade, often without anyone noticing.

Static best practices are problematic in two ways. First, they will put your staff on autopilot, which dulls creativity. Second, they aren’t optimized for maximum success today. They continue to rely on what worked last week, last month, last year.

Don’t use what you learn to create rules; use what you learn to push your team into even more exciting experiments. When you adopt a practice of continuous experimentation and curiosity, innovation will follow.

The science man and innovator, Fernando Fischmann, founder of Crystal Lagoons, recommends this article.

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