Questions are powerful.
 
When we want to move forward in life, to conquer some challenge or achieve a goal, or survive, we’re asking ourselves questions:
  • How did this happen?
  • What can I do? How can I fix/achieve/avoid ____?
  • What are my options?
  • What will work? What won’t work?
 
Situations that require decisive action stress us out. Most of the time we react rather than act. When many reactions are possible, we balk. When we have to be proactive rather than reactive, we seek assurance that our decision is a good one. So we ask ourselves questions, then choose what seems to be the best answer and act on it.

When the best answer isn’t good

What happens if our best answer isn’t a very good one?
 
All too often, we’re acting on our best answer but our best answer is, frankly, awful.
 
This matters because our answers determine the quality and effectiveness of our actions. Of course, they’re not the only factor: how well we execute also matters. But poor answers, even when executed well, still give terrible results.
 
When things don’t work out the way we want, how often do we revisit our answers?
 
Most of the time, we don’t.
Instead, we criticize ourselves. We see our mistakes, our weaknesses, our errors, our failures in execution. We blame ourselves and our poor execution for lack of success.
 
Sometimes poor execution is the problem. But sometimes it isn’t. Many times, the execution is adequate. It’s the poor answer that’s the problem.

How to get better answers

To raise the quality of our decisions and actions, we need to raise the quality of our answers. To raise the quality of our answers, we look at the questions we’re asking.
 
We learn to ask better questions.
 
Questions provide the framing, the structure for our answers. We have to focus our attention, and to do that we need boundaries. We need to define what’s relevant and what isn’t. Many questions, however, provide a shoddy structure. They put the wrong boundaries in place, focus the attention in the wrong direction, or cut off relevant options arbitrarily.
 
If you’ve attempted to reach a goal or solve a problem multiple times without success, stop and look at your questions.
Chances are high that you’re asking the same questions on every attempt, then executing slight variations of the same best answer every time. Of course you’re not making progress. You’re not changing anything.
 
Asking different questions can show us what to change. Different questions open up new options and methods. Better questions get us to better answers. Better answers—executed adequately—change our results.

How to ask better questions

1. Start noticing the questions you ask yourself.

Bring them out into the world of the sense where you can see, hear, and assess the questions. Unspoken questions (i.e., those we ask internally only) are often negative, limiting, and based on false assumptions. Speaking them—either verbally or in writing—makes it easier to see the problems with a question and start looking for better questions.

2. Start modifying your questions.

Sometimes it’s difficult to come up with brand-new questions. Instead, make changes to the questions you already ask:
  • What am I going to do? ➡ What options do I have?
  • How bad can this be? ➡ How good could this become?
  • How did this happen? ➡ How can I benefit from this happening?
  • What did I do to deserve this? ➡ What can I do to improve this?
  • How can I possibly handle this? ➡ How much of this can I safely ignore?
  • What will people think? ➡ Who can give me sound advice?

3. Look for new questions to ask.

There are two sources: people who are doing well in the relevant area, and people who aren’t. You can get new questions from successful people or unsuccessful people. From experts or amateurs.
  • Copy the questions from the successes, from the experts, from those who have successfully applied wisdom to achieve their goals. They’re probably asking better questions than you. Find out what those questions are, then start using them.
  • Avoid the questions from the unsuccessful. Compare them to your own questions. Do you see patterns of negativity, blame, limitation, victimization, helplessness, scarcity, etc.? Those are the patterns to remove.

4. Look for both internal and external insights from your questions.

Some questions are internally focused: how do I feel about this? What do I fear in this situation?
Some questions are externally focused: What tactics can I use? What resources am I not aware of?
Use both kinds of question to get a bigger, balanced picture of your options and obstacles.

Questions to start using

Here are some questions you can start using now. They’re usually most helpful when you make them specific to your situation.
For example, instead of asking the first question as-is, include the specific situation or goal you’re facing: What will happen if I succeed in this thing I’m currently attempting?
That gives you a more focused question, which will (generally) result in better, more helpful answers.
 
Note: Each question has multiple versions and/or spin-off or going-deeper questions. You don’t need them all. Keep asking until you get some answers that feel new, more expansive, more helpful, or more insightful in some way. You’re seeking better understanding and improved options in the answers you generate. Keep asking until you find them.
 
  1. What will happen if I succeed? What are the positive results of success? What are the negative results of success? What scares me about success in this are?
  2. What is my big vision? What’s motivating about that vision? How did my vision originate? Where did it come from? How much of it is mine? How much of it is a copy of someone else’s vision? What do I want to keep? What can I discard? What’s weighing me down? What doesn’t fit? What is most exciting about it?
  3. What benefit am I getting by staying as I am? What’s the reward that keeps me stuck in this situation? How do I benefit from not changing? What in me wants to resist? What serves me in these patterns?
  4. What am I afraid of in this area? What’s the biggest risk? What’s are the smaller risk? Which risks frighten me the most? Why are they frightening? What’s the worst that could happen?
  5. How soon can I let myself win? How soon can I acknowledge my success? How many milestones can I put up? How can I measure progress in a way that’s motivating? How soon can I let myself be excited about my progress? Am I safeguarding myself from disappointment by not letting myself be excited? How can I change that?
  6. What have I done in the past in this area? Did it work? If yes, what exactly worked? How can I repeat what worked? How can I improve what worked? If no, what didn’t work, exactly? How can I avoid repeating it? Are there ways I am knowingly wasting my time? Are there ways I am mindlessly repeating patterns and habits that don’t help?
  7. Do I need more options or fewer options? Am I overwhelmed by choices? How can I reduce my choices? How can I quit reinventing the wheel? Am I optimizing when I need to be acting?
  8. What’s the simplest next step I can take? How can I lower the baseline for success in this area? What’s the minimum effort I can put forward and still achieve something?
  9. How can I make this easier? How can I make it simpler? How can I trim it down? What details can I remove? What standards can I let go of? How can I do it faster? How can I make it more fun?
  10. How can I increase the benefits and decrease the effort? Where are there opportunities to offset or decrease my energy cost? How can I trade energy cost for some other resource (money, help, partnership, accountability, systemization, automation, outsourcing, etc.)?
  11. Who’s my objective/trusted expert in this area? What are they saying? Who’s succeeded in this area? Who can share their wisdom with me? Can I trust them more than I trust my fears? How can I take their advice and test it? How can I take action on their wisdom right now?
  12. What’s the smallest slice I can eat from this pie? What’s my one-breath-at-a-time strategy in this area? How can I measure a day’s progress? What’s one action that guarantees forward movement? How can I most easily accomplish this action? How often do I need to take this action for it to have an impact?
  13. What’s not necessary? What am I doing that isn’t helping? What can I stop doing? What can I do less of? What details don’t make a difference? If I have to do only 20% of the plan, which 20% will I do? If I have to get this done in half the time, what would I change?

July 1, 2019