EXPAND OPTIONS BY LOWERING THE BAR FOR SUCCESS

Take the pressure off your partner by reminding them that they're not looking for the “right” option here—just a number of them. Bad ideas, one-chance-in-a-million schemes, and outlandish escapades are all fine.

Don't:

Do:

Another way to lower the bar for success is to ask the question: “What would you do if you didn't care whether you failed?”

EXPAND OPTIONS BY RECALLING PAST ATTEMPTS

Remind your partner of what they've already tried. Past attempts—whether successful or not—can provide insight on what might work going forward. The failed attempts can provide clues about what not to do and might suggest new paths forward by doing the opposite or simply a variation of the initial attempt. People often stop doing things that worked for a variety of reasons. It may be possible to incorporate a past strategy into the new plan.

EXPAND OPTIONS THROUGH WHAT-IFS

Sometimes people limit their thinking based on what they assume is possible. You can spur creativity through two different types of hypothetical questions.

The first type removes constraints. The second type adds constraints.

Dara used the first type in the conversation with Ben when she asked what he might try given an unlimited budget. When your partner is out of ideas, take away a limitation that you suspect might be curtailing their best thinking:

“What might you try if your budget were unlimited?”

“What could you attempt if you had all the time in the world?”

“What would you do if you were the only decision-maker here?”

“What would you do if you were sure your data were 100 percent accurate?”

How can adding constraints stimulate creativity? The history of entrepreneurship demonstrates that people can get very creative when resources are limited. When the obvious avenues are blocked, people are forced to come up with unconventional approaches that may prove far more elegant and effective than existing best practices.

Here's one example: Because of the pandemic, the Monkey Bar Gym in Madison, Wisconsin, was forced to close its facility. That's a constraint that could have shut down their business for good. What's a gym without a gym? But they chose a different option: They went online.

Co-owners Jon and Jessie Hinds now say they'll never go back to brick and mortar.

They're saving $180,000 per year in rent, accessing clients from around the world, and thanks to Zoom's gallery view, offering more personalization as they can give instant feedback on form to dozens of students at once. Their response to a massive constraint increased profits, improved the product, expanded their customer base, and reduced stress. Howie, one of those new clients, lives 1,000 miles away from their facility. He owes his new biceps to the power of constraints.

If not for the constraints created by the pandemic, Jon and Jessie Hinds would never have expanded their thinking—or their business.

When your partner is operating out of a stuck way of thinking, you can prime their creative pump by adding constraints:

“How would you approach this issue if you only had 15 minutes to deal with it?”

“What if you couldn't spend a single penny on theproblem?”

“What if you couldn't remove Ramona from the team?”

EXPAND OPTIONS THROUGH EMOTIONAL COURAGE CHALLENGES

Sometimes your partner will come up with options that lack variety and boldness. Is that okay, or should you push them to expand their range of options? The answer is, it depends.

Ultimately, your goal is to come up with a plan that offers a reasonable probability of success. If the magic of the new opportunity has suddenly opened up a whole new set of possibilities, they don't necessarily have to be “stretches” for your partner.

If, on the other hand, one of the opportunities is for them to develop their emotional courage muscle—to take more risks and do things that feel uncomfortable—then it's almost always fruitful to encourage them to think more broadly, bypassing the mental filter that screens out possibilities that don't feel “like them.”

When there's an emotional courage component to the opportunity, try asking some variant of the question, “What's the scariest thing you could try here?” That question is a great pattern interrupter because it's explicitly asking your partner to imagine an action beyond the scope of anything they would ordinarily consider.

Other questions to help your partner extend their creative planning into emotional courage territory include the following:

“What's an action someone would least expect from you?”

“What's completely off the table?”

“What is absolutely ‘undiscussable' here?”

“What's a truth that nobody's saying?”

“If you had an invisibility cloak and you could act or speak without being seen or recognized, what might you try?”

EXPAND OPTIONS THROUGH “OPPOSITE DAY” QUESTIONS

Another way to bust through limiting assumptions is to ask questions to identify options, not with the highest, but with the lowest probability of success. These “Opposite Day” questions can expand creativity in a number of ways.

First, they can be funny. Researchers Mark Beeman and John Kounios found that people were 20 percent better at solving creative word problems after watching a short Robin Williams comedy clip.

Second, they give your partner explicit permission to come up with “stupid” answers, which lowers the pressure and thus encourages risk-taking.

Third, often the opposite of a “stupid” idea is a good one. Back in the day, when Howie consulted with marketing clients who were completely stumped on how to increase website conversion rates, he'd remind them of the action they wanted visitors to take on a particular page, and then ask, “How could we make it less likely that they'd take that action?” They'd immediately be full of ideas: decrease the font of the key statements, move the “Subscribe” button below the fold, promise to spam anyone who entered their email, and so on. After a few minutes of this ridiculous exercise, the client had a long list of improvements, simply enacting the opposite of what they had just brainstormed.

Some ways to phrase the “Opposite Day” questions include the following:

“What definitely wouldn't work here?”

“What would be the worst way to approach this?”

“What option would provide the least value for the greatest effort?”

“How could you make the problem worse?”

EXPAND OPTIONS THROUGH LADDERING

Sometimes your partner's creativity can get hamstrung by the magnitude of the problem or opportunity. They may be trying to solve the whole thing, once and for all, in a single bound. One way to help them break free from all-or-nothing thinking is to introduce the concept of “laddering”—that is, breaking big climbs into modest, manageable steps.

You can help your partner identify rungs on the ladder in a few different ways.

One approach is to look at the energizing outcome as a project goal and list out the steps required to achieve it. Then order the steps chronologically, breaking them into achievable one-at-a-time chunks.

If the energizing outcome is to write a book, the first rung might be to write an outline or a description of the ideal reader (in this case, that's you, by the way) or a list of questions you want the book to answer. If the energizing outcome is Couch to 5k, the first step might be to be able to jog from one lamppost to another without stopping to walk.

A great “laddering” question is “What can you try this week to get into a better position next week?”

Another approach is to identify ladder steps based on difficulty. Just as someone who wants to get stronger will work with increasingly heavy weights as they increase their capacity using lighter ones, your partner can start with easier actions to build their skill and confidence for harder ones.

To someone who is afraid of public speaking, for example, raising their hand and speaking at the full company town hall may be too daunting to even consider. Speaking at a team meeting, or even a family reunion via video conferencing, might feel more doable.

A third approach is particularly effective if the goal is to change an ingrained pattern of behavior. In that case, they can ladder by picking specific moments and situations, rather than attempting a 24/7 transformation.

For example, taking a deep breath and pausing before speaking might be extremely difficult at night after a long day's work when a young child is being particularly unreasonable and demanding. But that same behavior might be much easier during a 10 a.m. conference call with an annoying colleague. By practicing during the conference call, your partner can develop habits and muscles that can be deployed in ever more challenging situations, including—eventually—evenings at home.