Seven questions for better decisions

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“Where should I put the ice cream?”

This is a real question I received from a teenager who was helping to clean up after a meal.

Questions like this come from fear of getting it wrong. Instead of thinking the problem through for ourselves, we imagine that there’s a “right answer” floating out there in the ether, and we give up and ask someone else when we don’t find it.

In work and life, success comes from the ability to make good decisions consistently. And good decisions come from clear thinking.

This skill is highly valuable. That’s why CEOs and moms get paid the big bucks. As a result of their strong decision-making abilities, they are the ones people turn to in a crisis. These leaders spend a large part of their day working to prevent crises in the first place. To do this, they are constantly assessing risk, weighing outcomes, and making predictions about the future based on the information they have.

In other words: Leaders think, they gather and weigh the options, and then decide. Some decision-makers have so much practice at this that it seems automatic. The grooves of clear thinking are so well-worn in their brains that they can come up with a decision so quickly it seems as though it was already there.

That’s why their colleagues, employees, students, spouses, and children rely on them so heavily for their wisdom — they always seem to have an answer.

However, that “answer” is an illusion. It wasn’t already floating out there — it’s really the result of quick and effective thinking and deciding. But we leaders have other important work, which is to guide our employees, students, and children to be strong leaders by giving them the opportunity to do this thinking and deciding, too.

This can be a painful process! We have to give them room to make choices, which means they may mess up. We have to accustom them to the discomfort of thinking (and being uncertain or wrong). At first, this is inconvenient, annoying, and time-consuming. But in the long run, we will be grateful to have others on our team who can think for themselves.

Here are some questions leaders can ask to help those they mentor to think through decisions:

  1. “Do you really need my input on this, or are you just asking me because it’s convenient?” I got this one from Wally Waldron, an entrepreneur and father of two. It’s blunt, but it helps people to realize that there’s no magic behind the curtain.

  2. “What is your desired outcome?” This question helps us to make sure that we are solving the intended problem. It is all too easy to make assumptions and completely lose sight of the goal.

  3. “How many solutions can you come up with?” Too often, decisions are framed as binary: right decision, wrong decision. It is freeing to realize that there are more possibilities out there, however outlandish some of them may be.

  4. “What are the potential challenges?” This question helps the aspiring leader push past the fear of making the wrong decision. By looking at the worst-case scenarios and figuring out how to handle them (or choosing the one that’s easy to live with), we can manage anxiety and take action confidently.

  5. “If you weren’t afraid, what would you do?” Fear leads to weak decisions. We’ve already dealt with our rational concerns; by taking irrational fears out of the equation, we can more clearly see the right call.

  6. Does it matter?” Sometimes, leaders are asked to make decisions that come down to opinion. “Should we get the blue one or the red one?” I learned from Derek Sivers that it is unwise for the boss to weigh in on things simply because she was asked. Asking, “Does it matter?” or “Are you seeking my opinion?” can help the people on your team to prioritize. It also challenges you, the leader, to wean yourself off of offering your opinion on everything.

  7. “What information do you need to make this decision?” Sometimes, we don’t even realize that we’re missing a key piece of data or that our decision is premature. And sometimes, the leader is, indeed, the one with the necessary information. Asking the decision-maker to reflect on what information is needed helps them to gain clarity about the decision. They’ll see that they need to either find what they need to know or postpone the decision.

At first, these questions may make your student, child, or subordinate uneasy or frustrated. But over time, they will begin to understand that by holding back on your own recommendations and encouraging them to make choices for themselves, you are empowering them and providing them with a lifelong toolkit that will increase their success and fulfillment — and yours.