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3 questions for anyone who says a problem is impossible to crack

The CEO of real estate and tech company Compass shares how to address problem-solving doubts and defeatism.

3 questions for anyone who says a problem is impossible to crack
[Photos: jose aljovin/Unsplash; Billy Huynh/Unsplash]
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When my mom would help me get ready for bed as a kid, she wouldn’t encourage me to have sweet dreams—she’d encourage me to have big dreams.

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Now, “dream big” may sound like obvious advice for entrepreneurs, owners of small businesses, and others chasing a better life for themselves and their families. But I am amazed at how rare it is for people to allow themselves to actually let themselves do it.

Dreaming big isn’t just a mindset; it’s an important skill. As CEO of the real estate technology company Compass, I’ve gathered experiences to refine my problem-solving skills and how I approach small and large challenges.  I’ve learned three questions that can help people overcome most problems, as well as encourage people to aim higher.

Can you prove that it’s not possible?

People frequently tell me that something we need to do can’t be done. My response is often, Show me that it’s not possible. I then follow up by saying if you can’t prove it’s impossible, then I believe it’s possible.

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This method, of trying to prove the impossibility of something, helps crystallize challenges in a useful way. For example, someone might say, “There’s no way we could launch an updated digital marketing tool for all of our real estate agents in two months. For both design and engineering, it would take each team two months to do their parts!”

The person hasn’t proven it’s impossible. In reality, they’ve just spelled out the problem they’ll need to solve to make a solution happen. To hit the tighter deadline, each team will have to move quicker and collaborate more tightly, working in parallel rather than waiting for the task to be handed to an outside team. This process may be hard, but it’s far from impossible.

Of course, if your manager asks you to fly to Mars at a speed faster than light, it’s fine to say, “That’s impossible!” Though even in this instance, it’d be more accurate to say, “Our current understanding of physics tells us that it is not yet possible.”

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What if this were your entire job?

The most common reason for people to think something can’t be done is they lack the sufficient time or personnel to realize the project. Often, there’s a sentiment there are too many other things to do. This is a legitimate concern, but it’s distinct from whether or not something is achievable. To bring this concept to the surface, I ask the question, “If this one problem or task were your entire job, how would you approach it?”

A framing like this frees the person to remove resource constraints and competing responsibilities, so they now have space to think freely about the problem. It reveals that “there’s no way we could do it” actually translates to “there’s no way we could do it with our existing team while also doing all of the other things we’re currently doing.” Once you’ve figured out the necessary steps, you can address the question of priorities and staffing of tackling the challenge.

What would you do if you had no other choice?

In pressurized circumstances, people can whip themselves into action to accomplish incredible things. Think of the stories of parents lifting extra heavy weights to rescue a child pinned underneath a fallen object. Think of people who are stranded out at sea or trapped by avalanches who somehow survive. Therefore, to get people into this solutions-oriented way of thinking, I’ll often ask: “Just for 10 minutes, pretend you had to do it. How would you go about it?”

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What’s so helpful about this framing is that it allows people to set aside (even if just for 10 minutes) the “I can’t” mindset and empowers them to think about how they would be able to make it work. It temporarily disarms the risk-averse part of our brains that wants to avoid exploring paths that feel challenging, uncertain, even dangerous. And the time boundary gives people the liberty to open up, knowing that they’ll soon be able to return to normal.

When people reply to this question, there’s often a bit of reluctance at the beginning of the answer (“Well, if I had to do it…”) that melts away mid-thought as they start to visualize and voice their ultimate actions (“…I guess I’d begin by writing a script to automate the most time-consuming part of the process”). Soon, you get that little hint of a smile when the “impossible” starts to feel possible to them.

It’s remarkable how many impossible-sounding breakthroughs we rely on every day—such as a supercomputer that fits in your pocket, a network that lets you search all of the world’s information in less than a second, and a multi-ton vehicle that shoots people through air. So, imagine how much more limited our lives would be if those inventors, designers and engineers had declared their exceptionally difficult projects “impossible” rather than finding out a way to make them happen.

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Robert Reffkin is the founder and CEO of the real estate technology Compass and author of the new book No One Succeeds Alone.