Outcrop Blog Post

Three creativity-boosting questions

In a creative slump? Ask yourself these three questions.

Time for a little honesty: how often do you say no to a suggestion without entertaining the possibilities? Nothing to be ashamed about, we all do it -- it’s how our brains are wired. Even in agencies, where the lifeblood of our business is creative solutions, it's so darn easy to shut down someone’s idea.

It almost feels good telling someone their idea wouldn't work, and crushing their contribution like LeBron James slamming away the opposing forward’s lay-up.

Trouble is, when it becomes the norm, employees stop contributing their ideas. Who wants to be shut down every single time?

Ideas are powerful, but we don't own them. In fact, the more we share them with supportive and thoughtful people, the more likely they'll grow. We may fear having our ideas rejected, or coming across as stupid or even someone else taking credit for our ideas, but we have to get over it. 

To do so, we need to change. Change our culture and our deeply ingrained habits.

So, how do we develop a creative culture in the workplace? For starters, we need to ask different questions. 

These questions are a good place to start. Ask them next time you hear an idea.

1. How might we...?

I was fortunate to learn this one from Dr. Min Basadur of Basadur Applied Creativity. It's part of his famous simplexity thinking process. 

First, you identify a problem. Then, you phrase it as a new challenge.

Let’s say you’ve just launched a product, Widget, but sales are sluggish after the first month. You investigate and find an insight: customers think Widget looks too much like the last product you launched -- three years ago.

Ask yourself “how might we position Widget as distinct from our previous launch?”

This question gets its power from its openness. Notice it doesn’t say anything about advertising a message. You don’t want to be too narrow, too soon.

The point is not to shut down any idea at this stage and save the judgment for later. Let yourself be dumb. Get all the obvious ones on the board.

It could look like:

  • advertise
  • redesign packaging
  • change name
  • remove old product from shelves

Narrow down the problem to open up pathways to more lateral solutions. Customers perceive the new product as identical to the old one. Maybe it looks similar; maybe the messaging isn't highlighting the benefits of the new product over the old. 

How might we emphasize the benefits of Widget in a simple way?

A message might not be the best solution. Remember what your high school English teacher said, "Show, don't tell." Of course, sometimes a message is the best solution.

How might customers perceive the difference between the new and old product?

This opens up possibilities beyond just an ad. You can try experiential marketing, set up an in-store display for customers to see and feel the difference. What if you set up a boxing ring and had the new Widget face off against the old version and kick its ass. That would be memorable. Could you make it a game for customers? An art installation?

Some of these won't work for your product. Some will be really stupid. But if you hold out on judging, your team will be more comfortable sharing ideas that might start dumb and later blossom into beautiful ideas.

2. Yes, and...

Technically not a question, this is a classic improv comedy rule that works by accepting another's idea with no strings attached, and continuing their line of thought. Judgement kills ideation. Don't hate, ideate.

Improvisation, whether comedy or rapping, activates almost identical parts of the brain associated with creative brainstorming. It involves shutting off the parts that inhibit and critique so unexpected insights can bubble up.

Next time you hear an idea, do your best to spur the chain of thought onward, to keep an idea alive even if you think it’s nonsense. Our goal is to become aware of the reflex to say “no.” You don’t have to actually say the words, you can think them.

Let’s use our Widget example from above. Suppose a team member suggests changing the name. You say, “yes, and we change the packaging to reflect the name.” This might be a terrible idea; the technique doesn’t always apply. What it develops is a positive and encouraging attitude toward ideas, and that’s always good for creativity.

3. What if?

This question opens up possibilities. It's the slogan of the misty-eyed dreamer, imagining a better world. If we could only chill for like five minutes, it could be a utopia.

What if we didn't say no by default? What if we didn't get stuck in mind-numbing meetings all the time?

As you can see, the possibilities are limitless.

It works beautifully because it doesn't attack, it doesn't judge; it barely even suggests. It simply asks for your brief consideration. Just hear me out for a second.

What if has a disarming effect, too. Rather than state a ridiculous notion as fact and cause people to hunker down in defense, it brings everyone to the same side. We’re in this together. Swatting away objections like it would never work and it's not in the budget is easy; you simply say, "well, what if it did?" and "what if it were?"

It’s hard to argue against that.

Ideas are rarely solidified at first thought. Thoughtful input is the key to nurturing it, to open doors and see what’s strong about the idea first. How could it work? Drop all  objections for a moment and take it towards its conclusion. Add to the idea before you take away.

You can go into decision mode afterwards and weigh the pros and cons and discuss challenges in advance. Everyone sees it from a different perspective, so they'll have something to add both positive and negative.


There are no rules when it comes to creativity. What these questions provide are tools to use when we need new ideas. It gets us to encourage and support one another first. There’s plenty of opportunity to rip apart ideas after. However, if you start the creative process with that approach, you’re guaranteed to end up with the same old baloney.

When we change our approach, we'll eventually change the way we work together. We’ll get to a place of more collaboration, new connections and better ideas. 

First we need to change how we treat our coworkers and their ideas. It’s tough, but it’s the only way forward.

-- Dean