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A scary good deal on trusted journalism
$0.99
per week
for 24 weeks
SAVE OVER $140
OFFER ENDS OCTOBER 31
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In questions, lie answers. That’s particularly true for decision-making.

In The Book of Beautiful Questions, journalist Warren Berger recommends thinking of your questioning skills as a flashlight and the decision ahead of you as a dark room. Every question illuminates a new area. The better the question, the more light it sheds.

We’re wired for gut decisions, but those can lead to traps. Here are four questions he offers to check up on yourself:

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  • What am I inclined to believe on this particular issue? Start by trying to articulate your beliefs.
  • Why do I believe what I believe? Nobel Prize-winning physicist Arno Penzias called this the “jugular question” because it forces you to consider the basis of your beliefs.
  • Why would I like it to be true? Wishing and hoping does not lead to great decisions.
  • What if the opposite is true? In an episode of Seinfeld, George Costanza found success by doing the complete opposite of what he would do normally.

That leads to four questions for further questioning your own thinking, which Mr. Berger calls the “intellectual humility questions:”

  • Do I tend to think more like a soldier or a scout? Julia Galef, co-founder of the Center for Applied Rationality, notes a soldier’s job is to protect and defend against an enemy, whereas a scout’s purpose is to explore and discover. “Making good decisions is largely about which mindset you’re in,” she says.
  • Would I rather be right, or would I rather understand? Wanting to be right leads to defensiveness and can wall you off from learning and understanding.
  • Do I solicit and seek out opposing views? Mr. Berger advises: “Don’t ask others if they agree with you – ask if they disagree and invite them to say why.”
  • Do I enjoy the “pleasant surprise” of discovering I’m mistaken? Finding out you’re wrong can lead to a feeling of shame. But you can also choose to embrace that discovery as a pleasant surprise, one of openness and growth.

Others may be urging you to take a certain course. Be wary. Use these five questions to wade through nonsense:

  • How strong is the evidence? Demand substance for every claim.
  • What are they not telling me? Sometimes the problem is not the information and evidence before you but what is being hidden.
  • Does it logically follow? When people are trying to persuade you, they may use flawed reasoning. This question helps to root out logical fallacies.
  • What is the opposing view? To strengthen your critical thinking, consider the opposing side of what is being suggested and try to weigh it with an open mind.
  • Which of the conflicting views has more evidence behind it? Choose that option.

Decision-making can call upon courage. Here are five questions that help you to overcome fear of failure:

  • What would I try if I knew I could not fail? This approach is used in Silicon Valley to identify bold possibilities.
  • What is the worst that can happen? This usually makes your fears less scary.
  • How would I recover from that failure? Realizing there are options for recovery can also reduce fear.
  • What if I succeed – what would that look like? This shifts from worst-case to best-case scenarios.
  • How can I step into the breach? Embracing baby steps can help you move forward.

And asking these questions can also help you to move forward – in the right direction.

Quick hits

  • To avoid wasting time in meetings that drag on, systems administrator Scott Matteson recommends aggressively booking them adjacent to each other  – if you have a 2 p.m. meeting, set another one for 1:30 p.m., guaranteeing you can only invest 30 minutes in it.
  • Get experience in two or three industries early in your career.  Consultants at ghSmart recently looked at how people rebounded after getting fired and found it helps to not be pigeon-holed into one industry when seeking a new gig.
  • Don’t use CCs on e-mail as a weapon. . Ottawa consultant Shaun Belding notes sometimes people will CC someone’s superior to send the passive-aggressive message, “Your boss knows I sent this to you, so you better not ignore it.” But that just creates friction between you and the other person.
  • If you’re always the smartest person in the room you have a big problem,   says consultant Steve Keating. You need to find a different room or fill it with smarter people, so you can learn and grow.
  • The answer to your quandary is often right there in front of you, hiding in plain sight, says entrepreneur Seth Godin. It just requires more work, risk or tradeoffs than you prefer.

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