Questions to ask yourself before a big decision

Guides · Updated October 26, 2026

Big decisions rarely go wrong because people didn't think hard. They go wrong because people thought hard about the wrong question, or didn't notice what they were assuming. These questions help you check your own reasoning before you commit.

Fifteen questions, in five groups

Work through them in writing. You won't need all fifteen every time. The ones that are uncomfortable to answer are usually the ones that matter.

Am I asking the right question?

• What exactly am I deciding, and by when? "Should I change jobs?" is a worry. "Should I accept this offer by Friday?" is a decision.
• What are all my options, including the ones I haven't considered? Most decisions get framed as yes or no. There is often a third path: wait, do part of it, or negotiate.
• What do I actually want from this? Name the outcome you're after. Sometimes a different option gets you there at a lower cost.

What am I assuming?

• What do I know, and what am I assuming? Write two lists. The second is usually longer than you expect.
• Where did my information come from, and what does that source want? Agents, recruiters, sellers and enthusiastic friends all have reasons to tell you a particular story.
• How do decisions like this usually turn out? Your situation may be special, but start from what typically happens to people in a similar position.
• What would have to be true for this to work? List the conditions, then mark which ones you have actually checked.

What could go wrong?

• Imagine it's a year from now and this went badly. What happened? This exercise, often called a pre-mortem, surfaces risks that optimism hides.
• What's the worst realistic outcome, and could I live with it? Not the disaster, the plausible bad year.
• Can I undo it? Reversible decisions can be made quickly. Hard-to-reverse ones deserve more time and more questions.

Am I thinking clearly?

• Am I choosing this because of what I've already put in? Money, time or pride already spent shouldn't decide what you do next.
• Am I being rushed, and by whom? A deadline set by someone who benefits from your quick yes deserves a question.
• What would I tell a friend in my position? Distance makes it easier to see what you're avoiding.

Who else matters?

• Who is affected, and have I asked them? Partners, family, colleagues. Their view is information, not just feelings to manage.
• Who knows something I don't, and how can I ask them? Find the person who holds the missing piece and ask them a direct question.

Many of these questions draw on the critical-thinking habits in M. Neil Browne and Stuart Keeley's Asking the Right Questions. The twelve habits DuoAsk trains are listed on the homepage.

Signs you're not ready to decide

If any of these is true, give yourself a little more time:

• You can't state the decision in one sentence. Get clear on what you're choosing before you choose.
• You've only looked at one option. Find at least one real alternative, even if you don't take it.
• Your main source has something to gain. Find a second source who doesn't.
• You're avoiding one question. If there's a question you don't want to ask, that is usually the one to ask.
• You'd be relieved if someone else decided for you. That's a sign you need more information or more time, not less.

How to decide once you've asked

Questions are only useful if they lead to a decision. A few habits help:

• Write the decision down with your reasons. It makes you clearer now and lets you learn later, whatever happens.
• Set a deadline that serves you. Not the one someone else set to hurry you.
• Decide what would change your mind. Name the evidence that would make you reverse course, before you see it.
• Make the first step small where you can. A trial, a partial commitment or a pilot keeps options open.

A good decision can still turn out badly. What you control is the quality of the questions you asked and the information you used.

When the decision depends on a conversation

Many big decisions turn on a single conversation: with an employer, a friend asking for money, a family member, a business partner. The questions you prepare for yourself are often the same ones you need to ask them.

DuoAsk lets you rehearse that conversation with an AI character who knows things you don't. Play one of eight stories, or describe your own decision and turn it into a scene. After you decide, you see where it led a year later and which questions you missed.

Stories to rehearse with

1. 1Quit for a full-time MBA$200k and two years for a ticket into consulting?Growth
2. 2A friend asks you to investYour old friend raises his glass: "I'm only short your $20k."Investing
3. 3A second café?The agent calls it the best spot in town. So why is it always for rent?Startup

Common questions